9.64 For each of the following reactions, provide a complete, detailed mechanism and predict the products, including stereochemistry where appropriate. Determine whether the reaction will yield exclusively one product or a mixture of products. For each reaction that yields a mixture, determine which is the major product. (a) OTs H3C (b) OTs H3C (c) OTs H3C NaCN (CH3)3CONA ? CH;CH,OH DMF DMSO (d) (e) CI CH3 (f) OTs H3C Na,CO3 NaOCH,CH3 ? CH;CH,OH, A CH;CH,OH, A CH3 DMSO, 95 °C

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9.64 For each of the following reactions, provide a complete, detailed mechanism and predict the products, including
stereochemistry where appropriate. Determine whether the reaction will yield exclusively one product or a mixture of
products. For each reaction that yields a mixture, determine which is the major product.
(a)
OTs
H3C
(b)
OTs
H3C
(c)
OTs
H3C
NaCN
(CH3)3CONA
?
CH;CH,OH
DMF
DMSO
(d)
(e)
CI CH3
(f)
OTs
H3C
Na,CO3
NaOCH,CH3
?
CH;CH,OH, A
CH;CH,OH, A
CH3
DMSO, 95 °C
Transcribed Image Text:9.64 For each of the following reactions, provide a complete, detailed mechanism and predict the products, including stereochemistry where appropriate. Determine whether the reaction will yield exclusively one product or a mixture of products. For each reaction that yields a mixture, determine which is the major product. (a) OTs H3C (b) OTs H3C (c) OTs H3C NaCN (CH3)3CONA ? CH;CH,OH DMF DMSO (d) (e) CI CH3 (f) OTs H3C Na,CO3 NaOCH,CH3 ? CH;CH,OH, A CH;CH,OH, A CH3 DMSO, 95 °C
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